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Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)(5) and Phenanthroline System

Title
Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)(5) and Phenanthroline System
Authors
Hwang, Joon YoungBaek, Jong HwaShin, Tae IlShin, Jung HaOh, Jae WonKim, Kwang PyoYou, YoungminKang, Eun Joo
Ewha Authors
유영민
SCOPUS Author ID
유영민scopus
Issue Date
2016
Journal Title
ORGANIC LETTERS
ISSN
1523-7060JCR Link

1523-7052JCR Link
Citation
ORGANIC LETTERS vol. 18, no. 19, pp. 4900 - 4903
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)(5)] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)(5), 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.
DOI
10.1021/acs.orglett.6b02375
Appears in Collections:
엘텍공과대학 > 화학신소재공학전공 > Journal papers
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